


The Crooked Kind

by woahhsailor



Category: Supernatural
Genre: Alternate Universe - High School, Anal Fingering, Anal Play, Anal Sex, Blow Jobs, Castiel's First Time, Dean's First Time With a Man, Eventual Smut, First Time, Hand Jobs, High School, M/M, Mutual Masturbation, Oral Sex, Slow Build, Smut, kind of fluff
Language: English
Status: Completed
Published: 2016-06-21
Updated: 2016-06-21
Packaged: 2018-07-16 12:19:01
Rating: Not Rated
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 6,061
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7267861
Author URL: https://archiveofourown.org/users/woahhsailor/pseuds/woahhsailor
Summary: <blockquote class="userstuff">
              <p>Castiel watched as his lab partner, who’d no doubt been eye fucking him since they started the semester a month ago, scribbled onto a piece of paper before folding it up and sliding it across the table. He looked down at the ripped out sheet beside his textbook and knit his eyes together before picking it up and reading the messy handwriting. ‘Do you want to fuck?’ followed by a smiley face. Castiel chuckled quietly before sticking the note into his trench coat’s pocket and looking back up at their teacher.</p>
            </blockquote>





	The Crooked Kind

**Author's Note:**

> Hey guys ! Sorry i havent posted in a long time . Life has been pretty rough the last few months , but im slowly getting back into it . This is based off a tumblr post i saw a few months back , i cant find it but if someone else can , please link me ! please excuse the mistakes , i dont have a beta and i'm pretty out of practice . i hope you enjoy ! i love you all ~

Castiel watched as his lab partner, who’d no doubt been eye fucking him since they started the semester a month ago, scribbled onto a piece of paper before folding it up and sliding it across the table. He looked down at the ripped out sheet beside his textbook and knit his eyes together before picking it up and reading the messy handwriting. ‘Do you want to fuck?’ followed by a smiley face. Castiel chuckled quietly before sticking the note into his trench coat’s pocket and looking back up at their teacher.   
  
He let a small smirk creep across his face as the other boy leant back in his chair, stretching his legs out. Dean Winchester was nothing but trouble, and Castiel Novak was only ever attracted to trouble. While his lab partner was looking at Lisa Braeden bending over in the front row, he scribbled out his phone number on a different sheet of paper and folded it.   
  
When the bell signaled that they were free to go, the whole class stood, and the two faced each other. Castiel tilted his head slightly to the side and confidently said “Subtlety isn’t your strong suit is it?” Dean smirked, cocking his eyebrow, and slowly shook his head back and forth. Cas grinned before handing the folded up phone number over to the other boy. With that, he turned on his heel and walked out of class.   
  
Castiel wasn’t the most confident person, but there was something about Dean that made him want to do crazy things. He’d just moved to Lawrence in August and he already knew about the Winchester’s. Dean was a hard ass who carried heat ‘for protection’, and his dad was locked up for abuse so he was raising his little brother.   
  
With that being said, that’s not why he was going to be bad for Cas. Dean had emerald green eyes, sandy coloured hair that occasionally stood on end, a chiseled jaw that ever so often had a dusting of stubble across it, the body of a greek god and a smile that made Castiel want to jump off of the nearest cliff. If you combine those good looks and the confidence that Dean has, nothing good can come out of it.   
  
Castiel finished the day with his head in a daze, still riding the high of Dean Winchester hitting on him. As he walked home from school all he could think about was if Dean _really_ wanted to have sex with him, or if it was a big joke. He checked his inbox multiple times on the short trek and gave up by the time he walked into his front door.   
  
After he made it into his bedroom, he tossed his phone and backpack on to his chair and flung himself back on his bed. He laid staring at the ceiling for what seemed like forever until his eyes fluttered shut. He sighed deeply as his eyes painted pictures of green eyed greek gods on his eyelids.   
  
Castiel had seen Dean shirtless as he ran around the track behind the school. His tan skin lightly glowed with sweat and as he turned toward Cas, he caught glimpses of a black chest tattoo. It was the only time that he’d seen Dean in anything but a tee shirt , a flannel and his leather jacket.    
  
As he laid and let images of the other boy dance in his head, he heard his phone vibrate against the wooden chair it was sitting on and immediately snapped out of it. He jolted off of his bed and grabbed it, fumbling to open his inbox.   
  
_Save my number, blue eyes. I don’t give it out to just anyone._  
  
Castiel grinned as a blush spread across his cheeks and tapped his fingers on his phone trying to think of what to say.   
  
_Don’t worry, i’ll keep it to myself. Cross my heart._  
  
And Cas meant it. He didn’t want Dean making anyone else feel like he makes him feel. Cas sighed before flopping back on his bed, this time with phone in hand. As he sank comfortably into the bed, his phone vibrated again.  
  
_I’ll hold you to that._  
  
Cas smiled at the text, wondering Dean’s true feeling for him. He’d been giving Cas googly eyes for months now, but had never spoke outside of classwork. Cas had tried to smother his crush on the other boy but every emotion he’d felt towards the older Winchester brother bubbled into his stomach, before the phone began to vibrate in his hand, signalling a phone call.  
  
“Errr, Hello?” Castiel asked confused  
  
“So, do you wanna hang out tonight or do I just need to keep my phone in my hand all night?” Dean Winchester’s voice flowed out of the phone like honey.   
  
“My parents are gone this week.” Castiel replied softly.   
  
“That’s not an answer, Mr. Novak.” As Cas’ last name rolled of Dean’s tongue, he felt a shock wave flow down his body and straight to his groin.   
  
“I lock my doors at 9. I’ll text you my address, _Mr. Winchester._ ” The black haired boy practically purred before taping his screen and ending the call. After his phone cleared he typed a quick message to Dean including his address and headed for the shower.   
  
After Castiel had showered , brushed his teeth , dressed in his pajama pants matched with a Star Wars tee shirt and dried his hair, it was six o’clock. He started to get nervous. What if he doesn’t show up? What if he showed up while I was in the shower? The questions ran circles in his head until finally he heard a knock at his front door. His socked feet padded across the cold tile and slowly pulled the heavy front door open.   
  
Dean was standing in front of him , similarly dressed in sweatpants and a Zeppelin shirt. His hand gripped the strap to the backpack slung over his shoulder. “Had to make sure Sammy ate his dinner.” He told Cas as he stepped in the door and toed his boots off.   
  
Cas softly closed the door after Dean was inside and dropping his things by the door. “Have you had dinner?” Cas asked nicely as Dean glanced into his large kitchen. The scruffy looking boy knit his eyebrows together, as if he wasn’t sure if he had or not. His stomach growled as he opened his mouth to decline and Cas smiled softly.   
  
“I haven’t either.” Cas said before walking into his shining kitchen. He knew Dean was probably staring. Most people didn’t know just how rich the Novak family was. Castiel’s father, Bartholomew, built his own company from the ground up and his mother Anna worked for Angelic Children’s Hospital. They were well off, to say the least.   
  
Castiel opened his refrigerator and glanced at his ingredient choices before moving to the nearby cabinets. He sighed deeply before turning to look back at Dean. “Mother doesn’t allow a lot of good food… but i’m in the mood for a greasy hamburger. You?”   
  
Dean’s face softened at the sound of a familiar comfort food and he nodded, a soft smile spreading across his face. He refused to admit it, but he was full of anxiety just being in Castiel’s house and it took him an hour of pep talk in the mirror to convince himself to come.   
  
Castiel smiled back as he watched the ease spread across the other boys face, and turned to grab a take out menu and his phone. “The Roadhouse has the best burgers in town, _and they deliver_!” He showed the menu to Dean who in turn busted out laughing.   
  
“Yeah, i want the double down with bacon and cheese, and a slice of Ellen’s pie.” He finally said after he calmed down. “I’ve been eating Ellen’s food since before the Roadhouse was built. Her daughter Jo and I grew up together. El’s like an aunt to me.”   
  
Castiel just nodded and dialed the number he knew by heart. “Hey, Ash?” He spoke into the mic. “It’s Cas, i want two of my usual.” Dean’s eyebrows shot up when he heard the words ‘my usual‘. “Erm,” he tapped his chin. “I want a root beer and a….” Cas let his words trail as he looked to Dean for his drink order.   
  
“Beer.” Dean said shortly.   
  
“And a coke.” Castiel said to the man taking his order. “Don’t forget my pie this time!” He said with a laugh before hanging up.   
  
Castiel looked towards Dean, and knit his eyes together. The other man looked at Cas like he grew three heads. “How often do you eat there?” He finally spoke.   
  
“Oh, uhm, I sneak it often when mother and father are gone. So a couple of times a month?” Cas replied before digging in his pocket and pulling out exact change and a tip for whoever delivers.   
  
Dean simply nodded before glancing towards the sofa in Castiel’s family room. Cas caught the other man’s eye wander towards the plush seating. “Want to go through the movies and find something to watch while we eat?”   
  
Dean smiled and nodded before padding across the tile floor in his socks towards the large case displaying DVDs.  Cas couldn’t help but fill with butterflies as he watched the man who he considered a Greek God standing in his pajamas looking for movies to watch with dinner together. All of a sudden Cas was filling with anxiety.  
  
‘Am I really about to do this? Am I going to have a one night stand with Dean Winchester? I’m going to lose my virginity to someone who doesn’t even care. What the unholy fuck are you doing Castiel James Novak.’ He thought to himself before hearing his doorbell chime out through the house.   
  
He walked towards the large front door, shaking the thoughts from his head. As he opened the door with a smile, he saw Jo Harvelle staring back at him. “ Hiya, Jo. “ Cas said nicely, before handing her the neatly folded money.   
  
“Why is Dean’s car in your driveway?” She asked him firmly. “Is he in there? Dean Samuel, What the hell are you doing?!” She yelled towards him, when he met her eye.   
  
“I’m eating burgers and watching Star Wars, what are you doing here Joanna Beth?” Dean snapped back, his green eyes turning to frustrated slits.   
  
She handed the food and drinks over to a frozen Castiel, and walked inside. “Uh….” Castiel trailed off.   
  
Jo shoved her finger in Dean’s face, while an angry look crossed her own face, before the two burst into a fit of giggles. The sandy haired man stood to hug the pretty blonde, while Castiel still stood frozen at the door.   
  
“I’m sorry, Castiel. Dean’s like family to me, and we tend to pick on eachother.” Jo said when she pulled away from Dean’s embrace.   
  
Cas sighed with relief before toting the food into the family room. Jo smiled softly before speaking again. “You guys enjoy, and Dean, don’t do anything I wouldn’t do.” And with that, she turned on her heel and headed back to the door.   
  
“That doesn’t leave much for me to do Jo.” Dean said with a chuckle as the girl shut Cas’ heavy front door.  “Sorry about her, she’s a bit off her rocker.” he said, looking back to Cas.  
  
“It’s okay, completely unexpected.. But okay.” Castiel replied setting the food on the glass coffee table before going back to the kitchen to grab a couple of plates.   
  
“Hey! Where’s my beer?” Dean asked when he realize that there were two cups of soda.  
  
“Dean, you are 19. I’m not ordering you beer.” Castiel said with a laugh, setting the dishes on the table and sitting, crossing his legs in front of the couch.  He pulled out each paper wrapped burger slowly, setting them on their respective plates, following with the fries, and then finally two wedges of plastic wrapped cherry pie.   
  
Dean sat silently on the couch, Castiel on the floor next to him, before realizing the movie needed to be started. He fumbled with the remote to press play while Cas was divvying out the food. The smell was driving him nuts, he didn’t know when the last time he ate was. He left all of the food in the house for Sam, and he didn’t have money for lunch at school. When Cas slide the plate to him, he began to slowly savour the fries, one bit at a time. He tried to bite back a moan around the food in his mouth, but it was so good, he made a low “mmmmm” in his throat.   
  
The sounds Dean was making eating left little to the imagination, and Cas was beginning to turn red in the face while the other man made guttural moans around his food. Cas shifted where he was sitting to keep from growing any harder at the sounds and distracted himself with his own food.   
  
After both of the boys finished eating and talking through their movie, it was nearly 9 o’clock, Cas was snuggled up against Dean’s leg on the floor and Dean was lazily running his fingers through Castiel’s hair from his seat on the couch. It seemed so natural even though the boys had been nothing but lab partners up until this point. Cas was relieved that Dean hadn’t just come over to fuck him, and then leave. It gave him this deep feeling of hope in the other man.   
  
Castiel couldn’t sit on the floor any longer and finally stood up, his joints cracking as his did. He stretched out, pointing his arms to the ceiling and half moaning from the relief. After he was done, he joined Dean on the couch. Dean wrapped his arms around Castiel’s shoulders and Castiel leant his head on Dean’s chest, listening to his heart pick up pace. At least he wasn’t the only one that was nervous about this.   
  
Dean softly, and slowly traced his fingertips along the skin just below the sleeve of Cas’ shirt, and the feeling was almost enough to put the dark haired man to sleep. Cas moved his hand to rest on Dean’s chest, the fabric of his soft tee shirt pulled tight.   
  
Dean smiled at the warm feeling that spread within him, it was such a lovely feeling, and as Cas’ hand rested on his chest, he turned to press a kiss to the other man’s forehead. He only realized what he’d done when the other man froze. Dean panicked for a moment, thinking he’d fucked up and tried to pretend that nothing happened, when Cas looked up to him.   
  
Castiel’s sapphire eyes stared deep into Dean’s emerald eyes, until he felt like he may fall into them and never find his way out. Before he chickened out, which he knew was going to happen, he leant up and pressed a soft kiss against Dean’s lips. He felt the other man tense up, so he pulled away. Dean stared into Castiel’s eyes again, before  returning the kiss.   
  
This time, Dean’s lips were soft against Cas’ own, spread just enough to lick his tongue along Cas’ lower lip. The dark haired man cupped his hand to Dean’s cheek and pressed into the kiss. Castiel wouldn’t admit it, but he’d never been kissed before. If this is what it felt like, he was sure that he would gladly spend the rest of his days doing it. The scruffy haired man tasted like citrus and vanilla, and he had the pleasant smell of leather twisted with black coffee and motor oil. Cas couldn’t get enough of it.   
  
He pressed his mouth harder against Dean’s, crawling into his lap from his place beside him and straddling the other boys legs. Dean made a let a soft, low moan escape his throat when he felt the dark haired boy press into him. When Castiel finally pulled back from the kiss, he pressed his forehead against his partners and smiled. The emerald eyed boy reciprocated the smile before wrapping his arms around his partners waist.   
  
“I didn’t know you were gay.” Cas finally spoke.  
  
“Hmm, neither did i.” The other man replied with a light hearted laugh before playfully tightening his grasp and nibbling on Cas’ neck, causing the younger man to dissolve into a fit of giggles.   
  
“It’s getting late.” Cas told him softly, running his thin fingers through Dean’s soft sandy hair.   
  
“I’ll-uh, I’ll crash on the couch.” Dean replied moving his hands to rest lightly on top of Cas’ thighs.   
  
Castiel just shook his head in response, before standing in front of the other man and extending his hand for Dean to take. Dean’s eyebrows knit together before taking his hand and letting him pull him up to a stand. Castiel silently lead Dean by hand up the staircase. Once to the top, he silently pushed a door open and Dean realized the were standing in his bedroom.   
  
Dean looked around for a moment, taking in the room. There was virtually no mess, no dirty laundry on the floor, no dirty plates on the desk in the corner. Everything had a clean shine to it, even the large bookcase filled top to bottom in hardcover books. His bed was made neatly and the only thing that didn’t seem to have a place was the laptop on the foot of the bed. Cas noticed it, and sat it in his desk chair, before turning the blanket down so both men could get in.   
  
Dean silently watched as the dark haired man climbed onto the bed and crawled under the duvet, finally settling against the wall. Cas silently patted the bed next to himself as an invitation for Dean to join, which he did.  
  
“Dean, what are we doing?” Cas asked softly, his head propped up on his hand, his elbow bent.   
  
“Well, it seems to me, that we’re laying in bed together.” Dean replied, turning on his side to face the other boy.   
  
Cas scoffed before speaking. “ I know that, smart ass. But, what are we doing lying in bed together? I mean, up until tonight… scratch that, even tonight, we haven’t spoke much and now we’re in bed together after making out on my parents couch.”   
  
“Yeah, i’ve wanted to do that for months.” Dean replied, his voice studded with anxiety. “I mean, look at you, Cas, you’re gorgeous. I just never knew how to bring up a conversation with you. When i handed you that note I was just expecting you to toss it, but you seemed pretty willing when you gave me your number.”   
  
Dean let the words fall between the two of them before speaking again. “I wasn’t expecting to come over and have sex with you. Honestly, i was expecting to be turned away at the door, but i did have a good time tonight. It’s been a long time since i’ve been able to just sit and hang out with someone and them not expect more from me. For some reason i’m known to be this big man whore, when i’ve only had sex once. I don’t exactly understand it.”   
  
“Well, i’ve never heard you called a man whore in so many words.” Cas replied with a light chuckle. “You really weren’t expecting anything from me tonight?” He asked softly, to which Dean shook his head.   
  
“No. I mean, i’ve never even been with another guy, I wouldn’t even know what to do.” His green eyes were somehow glistening in the dark room.   
  
“I could always teach you.” Cas said half jokingly.   
  
“How much do you know exactly, Cas?” Dean questioned the other boy.   
  
“Not much,” he shrugged. “Just what the internet has taught me and i’ve tried myself. I’m still a virgin.” Cas laid the hand that wasn’t holding his head up on Dean’s chest, feeling the rise and fall of the boy’s breathing.   
  
“What have you tried on yourself?” The other man asked, and Cas could hear the amount of nervousness in his voice.  
  
“Would you like me to show you?” Cas asked softly, moving his fingers on Dean’s chest, waiting for an answer. After what seemed like an eternity, he watched the other boy nod in the darkness. “May i kiss you again?” He asked, bringing another nod from his partner.   
  
Cas softly ran his hand from the other man’s chest up to his cheek, feeling the stubble beginning to prickle up there, before leaning in and pressing his lips against Dean’s again. Dean moved his hand to rest softly on Cas’ hip bone, before deepening the kiss. Cas let his tongue softly brush against Dean’s lower lip before the other boy opened his mouth, allowing Cas entrance. As Castiel softly licked into Dean’s mouth, he could hear Dean softly breathe his approval.   
  
Castiel allowed himself to lick and kiss Dean’s mouth, as the emerald eyed man began to softly gasp. He softly ran his hand back down Dean’s chest, his fingertips brushing softly against a hard nipple, causing the other man to arch his back slightly, before moving farther down. As Cas reached the waistband of Dean’s sweatpants, he pulled back from the kiss to ask approval.   
  
As Dean nodded, Cas slowly crept his fingers into the fabric on top of Dean’s boxers. When he ran his fingers across Dean’s slowly hardening cock through the thin fabric, he could feel the other man jolt from the sensation. Slowly, he leant back into the kiss, Dean snaking his hand around the back of Cas’ neck to settle his fingers at his hairline.  
  
Cas slowly began to run his open hand along Dean’s boxered length, causing the other man to breathe in deeply. “Is this okay?” He asked softly against Dean’s lips. Once Dean, again, nodded his approval, Cas dipped his fingers into the waistband of the other man’s boxers. When Dean felt the cool palm of his partners hand on his throbbing cock he jolted out of pleasure, and he swore one touch from Cas’ hand felt way better than sex with any female ever could. Cas was almost certain that there was no way in hell a 19 year old should have such a large cock. While pawing at Dean’s length, the burning desire in the pit of stomach grew at the thought of how large he really was.   
  
Cas wrapped his hand softly around Dean’s dick and began to slowly caress him. Dean, overwhelmed with pleasure pulled back from the kiss, and laid on his back against the pile of pillows behind him. Cas took this as an invitation to pepper kisses down the other’s neck, while he continued to slowly pump his partner’s cock.  
  
Dean’s right hand gripped Castiel’s soft sheets while his right wrapped around Cas’ hand, and helped guide him, showing him exactly how he liked it. Once Cas had gotten the rhythm down, he quickened his pace, causing Dean to buck his hips, thrusting against Cas’ fist. After he knew he had begun to drive the other man mad, he stopped completely, pulling his hand away.   
  
When Dean felt the loss of the hand, he ‘humph’ed in protest, but Cas offered a soft reassuring ‘shhh’ before pressing a soft peck on his lips and sliding down Dean’s body. Once Cas was face to face with Dean’s hips and pulling his dick out of his pants, he knew he was done for. Dean was larger than Cas had initially thought. He took a deep breath in before wrapping his lips around the head of Dean’s cock, causing the other man to buck wildly beneath him. Castiel used one free hand to hold Dean’s hips firmly in place, while the other wrapped loosely again, around his shaft. As Cas began to move Dean deeper into his mouth, he matched the motions with his hand.   
  
Cas licked and sucked at Dean’s cock, while Dean braided his fingers into Cas’ jet black hair. Before Dean knew it, Cas was deep throating him, causing Dean to throw his head back and thrust his hips softly, feeling his dick slide into Cas’ throat. He was almost positive that he was going to lose his mind. Cas could tell that Dean was enjoying what he was doing, and it caused him to smile around Dean’s dick. As Cas was working his mouth from base to tip, he let his tongue lick the length, causing more shuddering convulsions to explode from Dean’s muscles and he knew the other man was going to cum soon.   
  
As Dean bucked his hips and grasped Cas’ hair, Cas quickened his pace, letting Dean’s dick hit the back of his throat before almost completely leaving his mouth again, his hand working in unison.   
  
“Cas, Cas please- “ Was all Dean could muster, before both of his hands gripped Cas’ sheets, one thrust and Dean was riding an orgasm. As he writhed and shuddered beneath Castiel, the dark haired man continued to suck and caress while Dean was shooting hot liquid down the back of his throat. When Cas was confident that Dean had nothing left to give, he sucked lightly one more time, before letting Dean’s dick pop out of his mouth and swallowed and then neatly tucked Dean’s dick back into his sweats .   
  
“Oh my god.” Dean whispered, sweat beaded on his brow and his previously tensed muscles completely relaxed.   
  
“Is… is that good?” Castiel asked quietly while Dean continued to pant.   
  
“You’re going to have to teach me how to do that.” He finally spoke, completely breathless, a smile creeping across his face.   
  
Cas just smiled and nodded, shifting to a sitting position, his pants tented in the crotch. He’d enjoyed sucking Dean off as much as Dean enjoyed being sucked off. He grimaced a bit, pulling the sticking material away from his skin. Dean watched as Cas shifted uncomfortably, and couldn’t help but feel bad knowing that he didn’t reciprocate.   
  
“Cas?” Dean asked softly, looking him straight in the face.  
  
“Hmm?” Cas responded, trying to think of anything and everything to get his erection to settle down.   
  
“Ca… Can i try?”   
  
The question shot waves through the dark haired man, and he slowly nodded his head. And, with that, Dean scooted closer to Cas, before softly pushing him back on the bed. Dean leant over him, and kissed him softly on the lips and then proceeded to pepper kisses from the other man’s lips, down his chin and across his jaw to his neck. When Dean heard Cas let soft sighs escape his mouth, he continued down his throat and tee shirt covered chest, before rubbing Cas’ erection on top of his sweat pants. As the emerald eyed boy palmed at his partners cock, he continued to kiss lower and lower until his mouth met Cas’ waistband.   
  
Dean looked up to Cas for some kind of sign, telling him to continue. Instead, he was met with Cas’ eyes closed and lips slightly parted, which he took as invitation. Slowly he pulled the waistband of Castiel’s sweat’s down, causing his cock to spring out. Dean eyed Cas’ length, gulping silently at the sight. He’d never been this close to another guy’s dick, and he was more comfortable (and more turned on) than he thought he’d have been.   
  
He took a deep breath in and slowly wrapped his lips around the head of Cas’ erection, causing a deep moan to escape Cas’ lips. He’d never had someone else touch him, and feeling of Dean’s warm mouth was going to cause him to go mad. As Dean began to slowly move his mouth on Cas’ cock, Cas was stuck between moaning and writhing beneath him and being shocked that Dean Winchester was in his bed, giving him head.   
  
“Oh, Fuck.” Was all he could say as Dean took almost Cas’ entire length into his mouth, causing Cas to writhe spastically. Dean held back a gag as the other man’s cock hit the back of his throat, and as he sucked back to the tip of his cock, he glanced up to Cas. He was met with an image that he never thought would strike him as beautiful.  The moonlight was coming in Cas’ window, only illuminating Cas’ body from the navel up. His torso was surprisingly muscular and almost every muscle was twitching with pleasure. His collar bones stuck out just slightly, his neck stretched out and his head was thrown back on the pillow with eyes shut tight.   
  
Seeing the way Castiel was responding to what he was doing, made him want to keep going, but Cas lightly tugged at Dean’s hair. Once Dean felt the light pull, he let Cas’ cock pop out of his mouth, and looked him in the eye.   
  
“Dean, kiss me.” Castiel almost begged, and Dean slowly slid up Castiel’s body, right between his legs. Their cocks were pressed tightly together, with only the thin fabric of Dean’s pants between them. Dean softly peppered kisses from Cas’ collarbones, up his jaw and finally to his parted lips.   
  
As their lips latched together, both men know they were a lost cause. They immediately dissolved into a fit of nibbles and licks, growling and moaning softly while Dean ground his hips in rhythm against Cas’.  Cas’ desire was taking over his physical being, the pit of his stomach halfway felt on fire, like he’d snuck into his father’s liquor cabinet again. He ran his hands down Dean’s covered back, and began to pull at Dean’s sweats, until they sat right below his taut ass, his cock free.  
  
Cas was too into the moment to think about the lube in his nightstand, so he spit in his hand before reaching between the two of them and simultaneously stroking their cocks together. His open hand was wrapped around them both as he thrusted up in time with Dean’s thrusts down, causing a wave of moans from the two men. Dean laid his forehead against Cas’, occasionally kissing him softly on the lips while he quicked his pace, thrusting down against his partner.   
  
“Cas.. Fuck, Cas...” Dean trailed off, his already rough voice, husky and thick with desire. “I want you.”   
  
Cas ground his hips up against Dean’s again, his hand still working to keep their cocks pressed together. “What do you want Dean?” He asked between soft pants, not knowing how long either of them would last.   
  
“You, inside… please Castiel” Dean replied softly, his lips only inches from Cas’.   
  
“Are you sure?” Cas asked shocked, stopping all movement between them. Dean nodded slowly before pressing a kiss to Cas’ lips.   
  
Cas used his free arm to reach over and open his nightstand drawer. Inside was an unopened box of condoms and lube, he quickly fumbled with the box, opening it with just one hand and snatching one out. He tore it open with his teeth and Dean pulled back far enough for Cas to roll it over his cock. Cas moved his hand back to the drawer, grabbing the lube and applying a dollop to his hand. He reached his arm around Dean’s body and softly applied the sticky substance to Dean’s asshole.   
  
He knew from porn that he needed to ‘prep’ Dean, so he slowly circled his finger around Dean’s hole, before pressing a finger inside, just to the second knuckle. This sudden feeling of pressure and pleasure shot through Dean causing him to moan out, and he shook lightly to keep from thrusting against Cas again. Once Dean was finished reeling from the initial feeling of insertion, Cas slowly pressed further.  
  
“Tell me if you want me to stop, otherwise, you’ve got to relax. If you want me to stop, just tell me to. I will stop immediately, okay?” Cas softly whispered into Dean’s ear, attempting to soothe the tense man.   
  
“Don’t stop, please don’t stop.” Dean responded immediately.   
  
Soon after, Dean finally relaxed and Cas slowly began to finger Dean’s tight hole. After the sandy haired man turned into a pool of moans, Cas slowly inserted his second finger. He continued to finger, and scissor his index and middle fingers to stretch Dean, while he started to grind their dicks together again.   
  
“Cas please, please, Cas, please.” Dean begged, his ass pressed tight against Castiel’s hand.   
  
“What do you want, baby, tell me.” Cas whispered into his ear, before licking and nibbling at his earlobe.  
  
“Please fuck me.” Dean finally moaned and with that, Cas withdrew his fingers, applied another thick layer of lube to Dean’s asshole and then his latex covered cock. Cas’ directed Dean on how to sit, and Cas pressed his cock right against Dean’s virgin asshole.   
  
“Are you ready?” Cas asked softly, afraid Dean was going to back out, or he was going to cause some kind of pain. As Dean nodded against Castiel, and both men gasped out loudly as Cas pressed the head of his cock inside. Dean, still straddling Castiel felt like fireworks had just gone off in front of his eyes and he slowly pressed down against Cas’ slick cock. After Cas was almost halfway inside, he pulled his cock back out to the tip slowly.   
  
Dean laid his head on Cas’ chest, kissing and licking at the skin as Cas began to press back inside, this time making Dean’s tight hole swallow his dick. As Cas bottomed out, they’d both relaxed and were thoroughly enjoying the slight pain that was laced with pleasure. The dark haired man slowly began to move inside of Dean, softly thrusting inside, before pulling almost completely out. Dean - knowing neither of them were going to last long as soon as Cas began to quicken pace, his head thrown back on the pillow, his fingers digging into Dean’s hips, slid his hand between the two of them to begin to pump his own cock.   
  
As soon as Cas felt Dean jacking himself off, a new thick feeling of desire flooded his body, and he began to thrust harder, deeper inside of Dean, matching the rhythm the sandy haired man was making with his hand.   
  
“I’m not gonna last!” Castiel moaned loudly, and Dean quickened his hand, knowing he wasn’t going to either. Castiel dug his fingers into his partners hips, only half pulling out before thrusting deep inside again. “ Fuck fuck fuck!” Castiel yelled, thrusting once more into Dean, as soon as he was completely inside, began to cum. He threw his head back, and tightened his grip in the other man, almost positive he was going to leave bruises. He attempted to try to ride out the orgasm, but almost immediately after he began to cum, Dean was shooting hot white spurts on to his own chest.  
  
“Oh my god.” Dean whispered, looking down at Cas. “You’re amazing.” Castiel smiled softly, pulling his now softening cock out of Dean, and removing the condom. As Cas was beginning to clean himself, Dean took his now cum covered tee shirt off, showing his tight torso.   
  
“Look, Dean I’m not ready for round two, and if i keep looking at you like…”Cas let the words fall as he breathed in deeply “....like that, i’m going to want to be back inside you.”   
  
Dean let the words roll in his ears, and immediately covered in a bright red blush, before almost collapsing next to the other man, pulling his sweats back into place. Cas smiled softly, pulling his pants back up to his hips and rolling over to meet the gaze of Dean. “What are we?” Cas asked softly.   
  
“Bound for life.” Dean replied with a sincere smile. “I mean, we both lost our virginity to each other. Does it have to have a name?”   
  
“Well.. see.. Dean..” Cas let the words fall between them. “I’ve had this crush on you since i moved to Lawrence.” He could feel a blush blossoming over his cheeks so he hid his face in his pillow.   
  
“Really? I had no idea…” Dean trailed off. “But… i’ve had this crush on you since you moved to Lawrence. Plus, you should probably stop hiding your face, i mean, you’ve already been inside me, do you really need to hide your blushing?”   
  
Cas lifted his head slowly before pressing a soft kiss to Dean’s lips. “Be mine, Dean Winchester.” He asked softly, looking into Dean’s emerald eyes.  


**Author's Note:**

> http://woahhsailor.tumblr.com/


End file.
